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Born in Camberwell, London,[2] Watson made his debut aged 17 towards the end of the 2002–03 season against Watford,[5] giving a good performance to keep his place in the side for the final four games of the season. He scored his first goal for the club at the start of the following season in a 1–1 draw against Millwall,[6] and gradually featured in the Palace side more regularly over the next few seasons, surpassing 200 appearances for the Eagles before his 23rd birthday.

In 2006, he was one of six nominees for the "League Cup New Talent Award", drawn up by the Football Writers' Association.[7] He was also named as Palace's "Young Player of The Year" at the end of the season,[8] and was rewarded with a new contract, keeping him at the club until 2009.[9]

At the outset of the 2008–09 season, Watson had one year left on his contract at Palace. The club reportedly offered him a new contract that would have made him Palace's highest-paid player, which was subsequently turned down. He also turned down a move to Nottingham Forest, who claimed he was demanding too high a salary,[10] amidst rumours that he was seeking an offer from Queens Park Rangers. However a move never materialised before the end of the summer, and Watson returned to the Palace side, scoring five times in just 18 appearances before suffering an injury in early December. This turned out to be Watson's last appearance for the Eagles.

In late January, Middlesbrough offered £2m for Watson and were expected to sign the midfielder, who underwent a medical examination.[11]Wigan Athletic entered the race to sign him late on, and were successful in securing the deal after matching Boro's offer.[11] He made his debut for the club in a 0–0 draw against Aston Villa on 31 January, and scored his first league goal for Wigan in the 2–1 away victory over Sunderland at the Stadium of Light.[12] On 23 March 2009 he followed this up with a goal in his next game at home against Hull City.

On 1 September 2009, Watson signed for Championship side Queens Park Rangers (QPR) on loan until January 2010. Watson then made his debut 11 days later on 12 September in a 1–1 draw against Peterborough United at Loftus Road. He scored his first goal for QPR in a 5–2 win over Barnsley on 26 September 2009.[13] Watson was sent off on 21 October in a 4–1 win over struggling Reading, serving a two match ban.

On 22 February 2010, Watson signed on loan for Championship club West Bromwich Albion, initially until the end of the 2009–2010 season.[14] He scored his first goal for West Brom against Preston North End on 20 March 2010.[15] Having not made a league appearance for Wigan Athletic during the 2009–10 season, Watson hinted that he would like to sign a permanent deal at West Brom if the club could gain promotion to the Premier League.[16] He was recalled from his loan early by Wigan on 1 April 2010.[17]

Watson made his return to the first-team on 4 April in a 2–1 defeat against Fulham, and scored in Wigan's 3–2 win over Arsenal at the DW Stadium on 18 April 2010.[18] He kept his place in the team for the rest of the season, finishing with five league appearances for the club.

Watson lost his place in the starting eleven at the beginning of the 2010–11 season, limiting his playing time for the first half of the season. He regained his place in the side after Christmas, and was a regular starter for the rest of the season. Now being deployed in a deep-lying playmaker role,[19][20] his impressive form in the second half of the season helped the team escape relegation and retain their place in the Premier League. In August 2011, Watson signed a new three-year contract at the club.[21]

Watson made his return to first-team action in May 2013 against West Bromwich Albion in a 3–2 away victory for Wigan, playing out of his usual position as a sweeper.[24] Watson scored the winning goal in the 2013 FA Cup Final against Manchester City, a stoppage time header that gave Wigan Athletic their first FA Cup.[25]

Watson joined Watford on 23 January 2015.[26] He made his league debut the following day in a 7–2 win over Blackpool.[27] Almost a year later, Watson scored his first goal for the Hornets, which he scored directly from a corner in a 1–2 loss at home to Manchester City. Watson was not awarded the goal until more than a week after the game, as it was initially recorded as a Aleksandar Kolarov own goal, before a Premier League panel awarded it to Watson.[28]

In 2018, Watson's contract was cancelled by mutual consent at the end of the January transfer window.[29]